


Hunting for love

by 14sweet



Category: Supernatural
Genre: Angel Castiel, Angel Gabriel (Supernatural), Crossdressing Dean, Cute Dean, F/F, F/M, Forced Feminization, Gabriel (Supernatural) is Loki, Jock Castiel, John Winchester's A+ Parenting, M/M, Parent Gabriel, Shy Dean, Top Castiel/Bottom Dean Winchester, at the beginning but not really, castiel is a mini loki
Language: English
Status: In-Progress
Published: 2015-08-20
Updated: 2015-08-28
Packaged: 2018-04-15 15:53:57
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 3,481
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4612566
Author URL: https://archiveofourown.org/users/14sweet/pseuds/14sweet
Summary: <blockquote class="userstuff">
              <p>Dean was standing in the kitchen looking through the window, watching his small family playing some sort of game, where Gabe was pretending to eat the kids and Cas was just standing there listening to Sam and Jess ramble about something. When suddenly their eyes met and his breath hitched just like the first time he had laid eyes upon the beautiful creature that was now his husband, he smiled to him, took the snacks, arranged his dress and went to the garden where he would wait for the rest of his family to arrive. After all it was the annual Novak-Winchester (Singer-Harvelle, etc.) barbecue. It all had started with a hunt.<br/>It was 12 years ago when this story began.</p>
            </blockquote>





	1. Bad news and a new start

**Author's Note:**

> I wanted to post this history when I have finished it, but I thought that I may as well pos-it and see how well you like it, so I know if I finish it or not. anyway please enjoy! every mistake is my own so very sorry for them, please leave kudos and comments I love to know what you are thinking of the story so far!

In the passenger seat of the Impala was a sixteen year old Dean drumming his fingers to the rhythm of ACDC blasting through the stereo while a twelve year old Sammy was sleeping in the backseat, which wasn’t surprising, after all he had fought with their dad for almost 24 hours straight, but as always they had been forced to leave all behind and start in a new place. Right now Dad was taking them to another lost town where they will be spending some time while he ganked whatever monster he was chasing this week. After a few more hours they arrived to a little house in the end of what looked like the nicest street they have been in a long time, the house wasn’t anything fancy quite the contrary it looked like it had been abandoned for years, if they were going to stay there for a while it would need a lot of work.  And by a lot he meant almost building it all over again, compared to the other houses they have passed it was a dumpster but when compared to shitty motel rooms, it probably was a palace. What can he say they not always could afford great places.

While driving john was thinking pretty hard, he didn’t know how to tell dean that he needed to pretend being a girl for the hunt, because he sure as hell couldn’t use Sammy as bait and there was no way in hell he was dragging an innocent girl and even a slimmer chance of him pretending to be the girl, just thinking about it made him shudder. He decided to stop in one of the towns malls they were passing to buy some clothes for dean. While both his sons were sleeping he stopped in a mall, he didn’t take them because they were going to throw a fit. Since he didn’t know which size dean was he decided to take the more form fitting jeans and t-shit his son owned and went to the store where he asked a girl to get him girl clothes in the same size the jeans and t-shirt were, he also asked for make-up and undergarments. The girl was very feminine looking so he told her to choose everything to her liking since he has no knowledge of girls fashion, the girl went crazy from happiness and asked a lot of questions about what his daughter looked like and he told her how dean was a fairly good looking girl with pretty long lashes, the greenest eyes ever, pretty freckles covered his fair and smooth skin, the fullest and pinkest lips and also his light hair which looked almost golden in the sun. He couldn’t stop from thinking that his son would make a very good looking girl. The girl chose clothes for him, he paid for them packed the impala, went for some new clothes for Sam and some other accesorios like shoes since dean will need some girl shoes and everything else they will need for the few following months. When he finished he went back to the car and started again their journey in hopes of arriving the next day to their new temporary home.

As he predicted they arrived the next day late in the afternoon, it was almost 9 o’clock so the streets were dark which was good with him that way nobody will notice them arriving. He ushered both boys into the house while he took the things out of the Impala and into the house.

Sam was extremely grouchy when dean woke him up by dad’s orders; He much preferred just carrying him inside but whatever.They both went out of the car and into the house Dean could see how Sam looked at the house his eyes lighted up he seriously was hoping  they would stay here and dean didn’t dare say it but he was hoping for the same. From inside the house didn’t look much better but at least the heat seemed to work and everything was furnished they even got 3 rooms which meant that they wouldn’t need to share. The only down was that one room was a girls room but hey Sam could take it since he already had the girly hair and all. They went downstairs running to their dad since he will be the one assigning rooms.

 When they reached him dean started saying “Hey Samantha they’ve got a girly room for you” Sam put his best bitch face on but before he could say anything his dad said in his best stern voice: “Actually dean, that room is for you” Dean was stunned no way in hell was he taking a girls room and Sam the little shit had the nerve to laugh, just when he was about to jump him for making fun of him dad said: “ And I am going to need your full cooperation in this hunt, you know how I have been chasing this thing for months now with no success” Dean was static dad would let him help  “Yeah, what do you need me to do?” now his dad looked regretful, maybe even shy. He wasn’t sure what his expression conveyed but he was quick to cover it and deadpanned “I need you to pretend being a girl for a while” Dean was flabbergasted, Sam was laughing now incontrollable “Dad! No! , why can´t Sam do it?  He already has the girly hair and the bitch face?”

 “Dean! You know perfectly that is very dangerous for Sam to help in the hunts, and Samuel stop laughing at your brother this is a serious issue and if you don´t stop laughing. I will have to punish you, are we clear?” That stopped Sam, not because dad was abusive or anything like that,  but he could give a damn good spanking.

“But dad that’s not fair I don’t wanna do it!” Dean was whining he knows but he really didn’t want to do this, but one look at his father revealed that this discussion was futile he had already made a choice. So he sighed and prepared for what was about to be his most shameful experience ever. “Okay dad I will do it, but how am I supposed to pass as a girl? I don’t have any girl clothes, and my hair” suddenly realization hit him “wait a minute that’s why you haven’t cut short my hair in almost a month?”

“Obviously dean, I have been getting ready for a while since I realized that the monster only went for girls that have some similar appearance to yours. I am really sorry son but I really need you and don’t you worry I have everything covered”

Sam couldn’t hold it in anymore “yeah Deanna don’t you worry you will make a really pretty girl with your long eyelashes and everything else” now he was laughing once again

“Sam stop it, and Dean I expect you to be a proper girl nobody and I mean nobody must know that you are a boy. Are we clear? And if somebody discovers it I will suppose it was you Sam who talked too much so you better help him”

They both gulped and now he was more preoccupied than ever because he couldn’t fail or Sammy would pay the price. They both said “yes sir”

“Very good now dean bring me here those bags I will cut your hair and you will decipher how to do your make-u then I will take some pictures to complete the papers I had already asked a buddy of mine to do  for signing you both in school tomorrow”

John gave Sam his new clothes and things for school, the kid was so happy, that went excitedly to his new room while John prepared dean for this new experience. He cut his hair that was now shoulder length with bangs, then showed him how to apply his make-up and how to tuck himself in his panties for nobody to notice his male parts. When dean finally got dressed, he admired himself and was stunned by what he saw. He was the clear image of Mary Winchester. John swallowed some tears and took the pictures to fill the blanks in the file of his new daughter Deanna Winchester.

Dean woke up the next day when his alarm sounded at 6 am he was so well rested, his bed was so comfortable and the panties and nighty he was wearing felt wonderful in his skin, of course he would never accept to have a thing for girl clothes, damn Rhonda Hurley and her panty fetish that now he shared and him wearing them now wasn't helping in the slightest with his morning wood. He was so horny but decided against doing anything about it so he went and took a really cold shower, he finished quickly, put on his make-up and some new pink lacey panties with a matching bra that made him look like he got some cleavage then he put on his clothes for the day that consisted of a white knee length skirt with long socks and his new boots  also a pink t-shirt with the words sexy wrote in big shinny letters in the center of his chest finally he put on a cool leather jacket with such a slim fit that made him look even more curly and fit. He took his back pack and went to make some breakfast. They all ate in silence after Sam had his big freak where he honestly thought dean was a girl. They arrived at school in time, John signed them up and left them while he went to a mechanic shop named singer auto repair where he was going to start working some hours.

They went for their respective classrooms but not before exchanging some reassurance words and their classic bitch and jerk even though this time Sam said that he was now the bitch which irked him.

He arrived at his history class when the last bell rang, he really didn't want to introduce himself. He was so nervous what if someone discovered him, but the teacher some pushy bastard named Balthazar who called him sweetie didn't give him any options. So he stood in the front of the class where he could feel all the appreciative glances the boys were giving him, he felt like a piece of meat, but there were a pair of blue eyes that made his heart race and his breath catch because the owner of those beautiful eyes was gorgeous, he had messy sex hair, chapped lips and a very lean body, he could fell his gaze penetrating him and then his tongue went out and over his lips and he couldn't help himself and followed the movement with his eyes then realized that he was staring and went fiery red,  he stuttered his name like a blushing virgin and was able to hear how the guys were blowing air trying to calm down their running hormones, the teacher thanked him and signaled a seat besides the handsome boy which name was castiel or cas how he decided to call him cause castiel was a mouthful. The boy was clearly not interested in her cause he didn't even moved his eyes from the  board, he felt his stomach drop and what the hell!  He wasn’t just dressed as a girl no, now he was becoming one.

When the bell rang signaling the end of the class he steeled himself and decided to talk to the handsome boy, but when he was going to open his mouth, he just looked at her with narrowed eyes and stormed out. He felt a hand on his arm and turned around to find himself face to face with a cute redheaded girl "hi _sweetie_  " and at that comment she totally waggled her eyebrows " my name is Charlie, don't pay any mind to Cas he is weird like that but is a nice person even though he is the king of the school so better not get into his bad side, anyway how you feel about having some lunch with me later?” what the.. was this girl just flirting with him¡? “We can talk about star wars and star trek you know?” how could she know that he liked them was she a witch, then he saw how her eyes were signaling his bag which was adorned with pins from star wars and star trek and well that explains it but before he could answer she kept talking. ” You seem the type of girl which I could be friends with also I will introduce you to the gang, well it’s decided I will see you at the cafeteria" and just like that she left, weird but hey she seemed really kind.

He went to the rest of his classes which he shared with ass-Cas, yeah he was an ass now. How could he reject him like that, he didn’t even listened to him the second time he had tried introducing herself. When lunchtime finally arrived he was exhausted, pretending to be a girl was pretty tiring also the looks he was getting from the boys and some hatred from the girls wasn’t doing him any favors. He had just arrived to the cafeteria when he heard a cheerful voice calling her name, it was Charlie who was expecting him to go and sit with her group, whatever since he couldn’t eat with Sammy he would go with them. When he arrived to the table she introduced Her to everyone 

“Deanna good that you decided to join me, I will introduce you to the guys they are pretty cool, you will see.” She then looked back to everyone” See guys this one is the girl I was telling you about, her name is Deanna Winchester and she had just moved here”


	2. Chapter 2

**Summary for the Chapter:**

> We get a little insight of Castiel's mind.

**Notes for the Chapter:**

> Thank you so much for your comments and your kudos they are really appreciated! Hope you enjoy this new chapter!!

chapter 2 Cas POV

Cas couldn't believe how much his life had changed since the great fall. A lot of Angels had abandoned heaven because of the war that Lucifer fall caused. Once they used to be a very United family but everything went to hell and all that remained were broken bonds and broken loyalties. Cas had been no more than a cherub when it happened, he had been the last angel God made before he vanished leaving his sons to deal with the awful war and the inexplicable thing that now cas understood was free will, of course he hadn't learned it all by himself in fact the one who taught him how to defend himself and accepted him when no one in heaven did was his older brother/dad Gabriel or Loki as he liked to call himself since he left heaven. That way he said nobody will bother them it was their own witness protectio program.

At first he couldn't understand how Gabriel had accepted so readily his trickster nature or his new title as a pagan god since it was against all he had learned in heaven, also at first he thought his father was being extremely cruel when punishing humans after all weren't they supposed to love them and learn from them but then when he had witnessed first hand which type of monsters humans and non-humans could be he couldn't help himself and decided to do the same after all he was doing a greater good helping the earth to be a better place just what angels should be doing instead of fighting each other. They had already spent a lot of years living amongst humans and pretending to be gods, that he couldn't identify himself anymore with the Angels, this was his new life and one better that heaven could ever offer for him after all none of his sisters and brothers showed him love ever and his real dad just left him all alone. To say he was resented with heaven was an understatement but he couldn't care less no more he was living with Gabriel and as tricksters they got to punish the bad guys and mess with heaven sometimes without ever being discovered, it was funny but sometimes it was lonely as well they missed the bright lights and heat that the heavenly host provided, every year he could feel how his grace got colder and a little darker only leaving his trickster nature afloat. He was missing his light, Gabriel said that one day he would find his light just as him had founded it with Kali his on and off girlfriend, she was all right and a great person if you didn't mess with her temper but Gabriel said that even if she was a goddess and not an angel her light even if not much was enough to bring fire and light to him that's why even when they just messed around they always came back with each other. He was already used to call her mom sometimes when they were having touchy feeling days, they were rare but they existed. In those days was when he yearned to find his light but it wasn't easy since he had never met someone whose light was bright or pure enough until she came. Her name was Deanna Winchester.

It came as such a surprise he had already surrendered even though he was still very young and Gabriel always told him that he was just being a drama queen because he was only a couple of centuries old whlie in human appearance he remained a teenager. Gabriel and him had been looking for their safe heaven for some time when they found this little town, which supernatural activity was so low that they decided to stay there for a while. eventually Kali started to hang with them more often, everyone in town thought her was his mom and just traveled a lot for work purposes or something like that.

Gabriel owned a little cafeteria/bakery/candy store all his guilty pleasures combined, it was the best in town no to mention the only one so they made great business not that they needed the money they were already rich enough to last at least another bunch of centuries but it was nice to have something to do in order to forget the pranks and the trickster life for a moment so Gabriel worked there and Castiel went to school like any other teenager would do. They had lived in the town for at least 3 years when she showed up one random day. She was so bright and so pure that he was dumbfounded he felt like a lighting stroke his heart when he met those beautiful green eyes, he could get lost on them they were so green and so big her eyelashes framed them perfectly her dirty blond hair and the freckles only made her look more angelic, she was so damn pretty that Castiel felt his grace reach towards her which was weird since he hadn't felt his grace reaching to anyone like that EVER and that was what made him lose his cool, of course in the exterior he had his poker face on but his insides were mushing it was ridiculous and if it wasn't enough he had to sit beside her. She smelled delicious like apple pie, vanilla, leather and like the fresh air it was so sweet and so refreshing he couldn't think straight and then she talked to him and that was when everything went to hell, because he couldn't answer he was so affected by her and he really didn't appreciated it so he did the first thing his instincts told him. He pushed her aside, he literally ignored her, it was for the best Or so he thought but he couldn't get her out of her head, the rest of the day he watched her, he could tell that he was creeping her out a little bit after all he was staring at her like a piece of meat and he glared to every boy in school that dared to look at her. She of course didn't noticed it and until he made a claim she was free game so the boys didn't pay him no mind. He wasn't going to claim her and if the king of school decided to maybe make her life a little more difficult than necessary for her to leave sooner, well nobody had to know that. And it wasn't like she wasn't making his work easier, she was already hanging out with the weird ones. He was really looking forward to see how much she would resist. He went home extremely excited, which was so rare but he was already thinking a thousand ways to mess with her. It was going to be so fun!!

**Notes for the Chapter:**

> I will very much like to hear what you think about the work, love you all!! And cas can be a little ass but don't worry in the end he will come around!! :)

**Author's Note:**

> Thanks for reading! and if anyone is reading A new and better life!? hopefully I will be posting the next chapter next week! :)


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